EP1005586B1 - Procede de recuperation d'acide formique - Google Patents
Procede de recuperation d'acide formique Download PDFInfo
- Publication number
- EP1005586B1 EP1005586B1 EP98939668A EP98939668A EP1005586B1 EP 1005586 B1 EP1005586 B1 EP 1005586B1 EP 98939668 A EP98939668 A EP 98939668A EP 98939668 A EP98939668 A EP 98939668A EP 1005586 B1 EP1005586 B1 EP 1005586B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formic acid
- free
- pulp
- bound
- treated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C11/00—Regeneration of pulp liquors or effluent waste waters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C3/00—Pulping cellulose-containing materials
- D21C3/20—Pulping cellulose-containing materials with organic solvents or in solvent environment
Definitions
- the invention relates to a method for removing chemically bound formic acid from materials with residues of formic acid resulting from industrial chemical processes or to which the formic acid is otherwise bound.
- Material to be treated may be, for instance, a material containing cellulose and/or lignin.
- a typical material to be treated by the method of the invention is a (cellulose) pulp obtained by formic acid cooking or some other fraction recovered from a process of this kind, for instance, a lignin fraction.
- formic-acid-based pulp In production of formic-acid-based pulp, some formic acid remains in the pulp both in a free form and in a chemically bound form.
- Formic acid bound chemically to the pulp is typically in the form of a cellulose formate. Bound formic acid is also found esterified in lignin. Chemical binding of formic acid takes place particularly in connection with cooking, evaporating, distilling and drying stages. In general, chemically bound formic acid is formed in the pulp and lignin in an amount of several per cents, for instance; 3 to 5% per dry pulp unit when strong formic acid with a concentration of 60 to 100% by weight is used in cooking.
- Washing with water is most generally used to remove formic acid from the pulp produced by the formic acid method. However, mere washing with water is not sufficient to remove the bound formic acid or to reduce its amount to acceptable levels.
- the acceptable amounts of chemically bound formic acid in a dry, unbleached pulp washed from formic acid are in the order of less than 1%, preferably less than 0.5%.
- Finnish Patent 85,510 discloses a previously developed method for removing bound formic acid.
- This method employs vacuum evaporation at an elevated temperature, whereafter the pulp is washed with hot water or stripped with steam.
- the temperature used in vacuum evaporation is typically about 70 to 100 °C and in steam stripping about 100 to 140 °C.
- the formic acid concentration is very high, whereby the amount of bound formic acid further increases.
- This bound formic acid is then removed at an elevated temperature with hot water.
- Drawbacks with the method are that its implementation is difficult, for instance, due to a vacuum evaporator required, and its energy efficiency is poor.
- High washing temperature exceeding 100 °C
- high washing temperatures exceeding 100 °C
- the object of the method of the invention is to eliminate the drawbacks of the prior art methods and to provide a method that is useful in industrial processes for removing chemically bound formic acid without having to use high temperatures exceeding 100 °C and with using normal pressure.
- the invention relates to a method for removing chemically bound formic acid from a material containing the same, in the presence of free formic acid, whereby firstly part of the free formic acid is removed by water washing from the material to be treated in order to adjust the formic acid content to a range of 3 to 20%.
- the method is characterized in that the chemically bound formic acid is allowed to react to free formic acid at a normal pressure, at a temperature of 50 to 95 °C, the initial content of free formic acid being 3 to 20% and the reaction time being 0.5 to 4 hours, whereby free formic acid catalyzes the conversion of bound formic acid into free formic acid.
- the percentages of content (%) given in the specification, examples and claims in connection with the present invention refer to per cents by weight calculated on dry, brown (unbleached) pulp.
- the free formic acid content being within said range of 3 to 20%, free formic acid acts as a catalyst enhancing the conversion of the bound formic acid present in esterified form into free formic acid. If the free formic acid content is too low (less than 3%) the catalyzing effect is not sufficient, whereas if the free formic acid content is too high (in excess of 20%) formylation reactions start appearing, whereby formic acid binding increases.
- the starting material used in the method of the invention may originate from any chemical process utilizing formic acid, in which process organic material, such as wood, is typically used as a raw material.
- process organic material such as wood
- Typical examples are pulps obtained from a formic-acid-based pulp cooking process, or other fractions, such as a lignin fraction, containing bound formic acid and recovered from similar processes.
- the starting material used in the method of the invention may also be other material to which formic acid is bound in esterified form.
- the material to be treated may also contain other lower carboxyl acids, such as acetic acid either in a free form or in a bound form.
- cellulose pulp When cellulose pulp is used as a starting material, it can be either softwood pulp or hardwood pulp, or as well pulp made from herbaceous plants, such as common reed or reed canary grass pulp.
- the material to be treated may also be pulp made e.g. from various agricultural waste materials, such as straw.
- the free formic acid acting as a catalyst in the method of the invention typically originates from the strong formic acid with a normal concentration of 60 to 100% used as a cooking chemical.
- the free formic acid may also originate from other processes relating to the use of formic acid, in which processes organic material has been treated with strong formic acid, or organic material containing formic acid has been evaporated, dried, distilled or pyrolyzed..
- the 3 to 20% content of free formic acid essential to the method is obtained by washing off part of the free formic acid with normal water washing first at a pretreatment stage.
- This kind of formic acid concentration can readily be arranged at the formic acid recovery stage in connection with the washing of pulp (typically counter current washing), when the pulp is in any case washed with (normally 30 to 70 °C) water.
- pulp typically counter current washing
- chemically bound formic acid cannot be removed, but it remains in the pulp typically in an amount of about 3 to 5%.
- the material to be treated having a 3 to 20% content of free formic acid
- an elevated temperature less than 100 °C, at normal pressure
- the free formic acid of the reaction mixture catalyzes the decomposition of the esterified formic acid to free formic acid and its removal from the material to be treated.
- the initial content of free formic acid is preferably 5 to 15%.
- the reaction temperature is 50 to 95 °C, preferably 80 to 95 °C.
- Normal pressure refers to the normal atmospheric pressure.
- the short reaction time of 0.5 to 4 h is sufficient to convert the esterified formic acid to free formic acid in the conditions in accordance with the invention.
- the short reaction time is substantial in view of the industrial usefulness of the method.
- the method of the invention is in practice preferably carried out in such a way that after a pretreatment stage, in which the free formic acid content is adjusted to a range of 3 to 20%, the temperature of the material to be treated is raised to said range (less than 100 °C).
- the reaction mixture is allowed to stay at this temperature for the reaction time required, i.e. typically for 0.5 to 4 hours.
- the free formic acid catalyzes the hydrolysis of cellulose formate to cellulose and free formic acid, whereby the cellulose formate in the material to be treated can be completely or almost completely removed therefrom.
- the pretreatment stage and the removal of bound formic acid are carried out arranged in connection with a commonly used multistage washing of pulp.
- esterified formic acid can be released from lignin or a material containing lignin.
- the method of the invention generally comprises an additional after-treatment stage, in which the formic acid released into the reaction liquid is removed from the pulp by water washing (typically at a temperature of 30 to 70 °C). Thereafter the obtained formic acid is supplied for regeneration and reuse.
- the chemically bound formic acid can be removed in a very simple manner by the method of the invention without having to use high temperatures exceeding 100 °C and complicated pressure equipment.
- the energy consumption of the method is low, and the effect on fibre quality is not deteriorating.
- the amount of bound formic acid can be reduced to acceptable levels within a time useful in industrial processes. Within two hours the amount of bound formic acid can be reduced to nearly 1% or less, and within four hours the bound formic acid can be removed completely or almost completely. On the other hand, it appears from the reference examples 4 and 5 that with excessively low amounts of free formic acid, acceptable levels are not yet achieved within two hours.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
Claims (5)
- Procédé d'élimination de l'acide formique chimiquement lié à partir d'une matière le contenant, en présence d'acide formique libre, caractérisé en ce que l'acide formique chimiquement lié est lié sous forme estérifiée, une partie de l'acide formique libre est d'abord éliminée par lavage à l'eau de la matière destinée à être traitée, afin d'ajuster la teneur en acide formique libre dans la plage de 3 à 20 %, après quoi on fait réagir l'acide formique chimiquement lié pour former de l'acide formique libre sous pression normale, à une température de 50 à 95 °C, la teneur initiale en acide formique libre étant de 3 à 20 %, et le temps de réaction étant de 0,5 à 4 h, de sorte que l'acide formique libre catalyse la conversion/transformation de l'acide formique lié en acide formique libre.
- Procédé selon la revendication 1, caractérisé en ce que la température de réaction est de 80 à 95 °C.
- Procédé selon la revendication 1 ou 2, caractérisé en ce que la teneur initiale en acide formique libre est de 5 à 15 %.
- Procédé selon l'une quelconque des revendications précédentes, caractérisé en ce que le procédé comprend en outre une étape de post-traitement dans laquelle l'acide formique libéré est éliminé par lavage à l'eau à partir de la matière destinée à être traitée.
- Procédé selon l'une quelconque des revendications précédentes, caractérisé en ce que la matière destinée à être traitée est une matière obtenue à partir d'un procédé de cuisson de pâte basé sur l'acide formique, contenant de la cellulose et/ou de la lignine.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI973474 | 1997-08-22 | ||
FI973474A FI108233B (fi) | 1997-08-22 | 1997-08-22 | Menetelmä muurahaishapon talteenottamiseksi |
PCT/FI1998/000635 WO1999010595A1 (fr) | 1997-08-22 | 1998-08-18 | Procede de recuperation d'acide formique |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1005586A1 EP1005586A1 (fr) | 2000-06-07 |
EP1005586B1 true EP1005586B1 (fr) | 2003-06-04 |
Family
ID=8549408
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP98939668A Expired - Lifetime EP1005586B1 (fr) | 1997-08-22 | 1998-08-18 | Procede de recuperation d'acide formique |
Country Status (13)
Country | Link |
---|---|
US (1) | US6252109B1 (fr) |
EP (1) | EP1005586B1 (fr) |
CN (1) | CN1100915C (fr) |
AT (1) | ATE242354T1 (fr) |
AU (1) | AU744767B2 (fr) |
BR (1) | BR9811343B1 (fr) |
CA (1) | CA2300114C (fr) |
DE (1) | DE69815354T2 (fr) |
DK (1) | DK1005586T3 (fr) |
ES (1) | ES2200360T3 (fr) |
FI (1) | FI108233B (fr) |
PT (1) | PT1005586E (fr) |
WO (1) | WO1999010595A1 (fr) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI108234B (fi) | 2000-02-28 | 2001-12-14 | Chempolis Oy | Menetelmä massan valmistamiseksi |
FI117632B (fi) * | 2001-07-13 | 2006-12-29 | Chempolis Oy | Menetelmä massan valmistamiseksi |
US7604967B2 (en) * | 2003-03-19 | 2009-10-20 | The Trustees Of Dartmouth College | Lignin-blocking treatment of biomass and uses thereof |
US8580541B2 (en) * | 2003-03-19 | 2013-11-12 | The Trustees Of Dartmouth College | Lignin blockers and uses thereof |
US8460901B2 (en) | 2010-05-18 | 2013-06-11 | Georgia Tech Research Corporation | Formic acid treatments of biomass feedstock |
FI123052B (fi) * | 2011-09-23 | 2012-10-15 | Chempolis Oy | Esikäsittelymenetelmä vesiliukoisten sokereiden tuottamiseksi lignoselluloosamateriaalista |
FI126451B (fi) * | 2014-12-23 | 2016-12-15 | Chempolis Oy | Prosessijärjestelmä kemikaalien erottelemiseksi, tislauskolonnijärjestely ja kemikaalien erottelumenetelmä |
CN105294164B (zh) | 2015-12-03 | 2018-01-19 | 歌尔股份有限公司 | 吸音材料颗粒的制备方法和吸音材料颗粒 |
FI130441B (en) | 2020-03-31 | 2023-09-01 | Chempolis Oy | Hydrolysis of cellulose esters |
CN112048933B (zh) * | 2020-09-07 | 2022-11-15 | 齐鲁工业大学 | 化机浆和半化学浆的生产方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI85510C (fi) * | 1990-05-29 | 1992-04-27 | Kemira Oy | Foerfarande foer aotervinning av laegre alifatisk syra. |
-
1997
- 1997-08-22 FI FI973474A patent/FI108233B/fi not_active IP Right Cessation
-
1998
- 1998-08-18 AU AU88096/98A patent/AU744767B2/en not_active Ceased
- 1998-08-18 CN CN98808384A patent/CN1100915C/zh not_active Expired - Fee Related
- 1998-08-18 BR BRPI9811343-7A patent/BR9811343B1/pt not_active IP Right Cessation
- 1998-08-18 AT AT98939668T patent/ATE242354T1/de active
- 1998-08-18 CA CA002300114A patent/CA2300114C/fr not_active Expired - Fee Related
- 1998-08-18 DE DE69815354T patent/DE69815354T2/de not_active Expired - Lifetime
- 1998-08-18 PT PT98939668T patent/PT1005586E/pt unknown
- 1998-08-18 DK DK98939668T patent/DK1005586T3/da active
- 1998-08-18 ES ES98939668T patent/ES2200360T3/es not_active Expired - Lifetime
- 1998-08-18 EP EP98939668A patent/EP1005586B1/fr not_active Expired - Lifetime
- 1998-08-18 WO PCT/FI1998/000635 patent/WO1999010595A1/fr active IP Right Grant
-
2000
- 2000-02-09 US US09/501,565 patent/US6252109B1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
AU8809698A (en) | 1999-03-16 |
CN1100915C (zh) | 2003-02-05 |
ES2200360T3 (es) | 2004-03-01 |
DE69815354D1 (de) | 2003-07-10 |
WO1999010595A1 (fr) | 1999-03-04 |
CA2300114C (fr) | 2007-03-20 |
AU744767B2 (en) | 2002-03-07 |
PT1005586E (pt) | 2003-10-31 |
DE69815354T2 (de) | 2004-05-13 |
FI108233B (fi) | 2001-12-14 |
DK1005586T3 (da) | 2003-09-22 |
US6252109B1 (en) | 2001-06-26 |
FI973474A0 (fi) | 1997-08-22 |
CN1267344A (zh) | 2000-09-20 |
ATE242354T1 (de) | 2003-06-15 |
BR9811343A (pt) | 2000-09-12 |
BR9811343B1 (pt) | 2008-11-18 |
FI973474A (fi) | 1999-02-23 |
CA2300114A1 (fr) | 1999-03-04 |
EP1005586A1 (fr) | 2000-06-07 |
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